Microbial biotransformation of some novel hydantoin derivatives: Perspectives for bioremediation of potential sunscreen agents

Abstract

Having identified novel hydantoin derivatives (compounds 1-5) demonstrating promising photoprotective capacity against UV radiation, and understainding the problem of the biotic and abiotic degradation of UV filters, the aim of the study was to evaluate their metabolic fate with the environmental fungus Cunninghamella echinulata. In parallel, compound 1 in vitro microsomal metabolic pattern was evaluated. Finally, in silico toxicity of test compounds and their biotransformation products was estimated, and parent compounds photostability was assessed. The study demonstrated the capacity for C. echinulata to metabolize 1-5, which were biotransformed to a greater extent than the standard UV filter. O-dealkylation of the side chains attached to the phenyl or hydantoin rings, and hydroxylation of the phenyl ring occurred during microbial transformation. O-dealkylation product was a unique metabolite observed in microsomal biotransformation of 1, being its intrinsic clearance in the medium category range. In silico study demonstrated that compounds 1-5 have low toxicity risk. Among the resulting metabolites, four can increase the risk of reproductive effects as shown by OSIRIS prediction. Noteworthy, all indicated metabolites belong to minor metabolites, except for compound 3 major metabolite. Moreover, the results of the photostability study showed that 1-5 were considered to be photostable. To sum up, the obtained in vitro biotransformation, photostability, and in silico toxicity results encourage further studies on hydantoin derivatives as potential UV photoprotective agents. The presented biotransformation profile of compounds 1-5 by C. echinulata suggests that these compounds may follow a similar biodegradation fate when released into the environment.

Keywords: Bioremediation; Biotransformation; Cunninghamella; Hydantoin derivatives; Toxicity; UV filters.